RU2265011C2 - Производные азотсодержащих гетероциклических соединений, способы их получения, фармацевтическая композиция на их основе и способы лечения воспалительных заболеваний и заболеваний дыхательных путей - Google Patents
Производные азотсодержащих гетероциклических соединений, способы их получения, фармацевтическая композиция на их основе и способы лечения воспалительных заболеваний и заболеваний дыхательных путей Download PDFInfo
- Publication number
- RU2265011C2 RU2265011C2 RU2002122100/04A RU2002122100A RU2265011C2 RU 2265011 C2 RU2265011 C2 RU 2265011C2 RU 2002122100/04 A RU2002122100/04 A RU 2002122100/04A RU 2002122100 A RU2002122100 A RU 2002122100A RU 2265011 C2 RU2265011 C2 RU 2265011C2
- Authority
- RU
- Russia
- Prior art keywords
- hydroxypropoxy
- acetamide
- phenyl
- pyrrolidin
- chlorophenoxy
- Prior art date
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- -1 of nitrogen-containing heterocyclic compounds Chemical class 0.000 title claims abstract description 164
- 238000000034 method Methods 0.000 title claims abstract description 44
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 23
- 201000010099 disease Diseases 0.000 title claims abstract description 19
- 238000011282 treatment Methods 0.000 title claims abstract description 18
- 208000027866 inflammatory disease Diseases 0.000 title claims abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 10
- 230000000241 respiratory effect Effects 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 239
- 239000000203 mixture Substances 0.000 claims abstract description 113
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 83
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract description 63
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 62
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 26
- 229910052717 sulfur Chemical group 0.000 claims abstract description 25
- 239000001301 oxygen Substances 0.000 claims abstract description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 19
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
- 239000003814 drug Substances 0.000 claims abstract description 11
- 230000000694 effects Effects 0.000 claims abstract description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 64
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 51
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 50
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 47
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 35
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 239000012453 solvate Substances 0.000 claims description 27
- 229920006395 saturated elastomer Polymers 0.000 claims description 26
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 13
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 13
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 12
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 11
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- NPSKGQWYPOEEPS-UHFFFAOYSA-N n-[2-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OCC(O)CN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 NPSKGQWYPOEEPS-UHFFFAOYSA-N 0.000 claims description 10
- 239000011593 sulfur Chemical group 0.000 claims description 10
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- 108700012434 CCL3 Proteins 0.000 claims description 6
- 102000000013 Chemokine CCL3 Human genes 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- OMCXZJNJUZNUPA-UHFFFAOYSA-N n-[4-cyano-2-[3-[4-(3,4-dichloroanilino)piperidin-1-yl]-2-hydroxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(C#N)C=C1OCC(O)CN1CCC(NC=2C=C(Cl)C(Cl)=CC=2)CC1 OMCXZJNJUZNUPA-UHFFFAOYSA-N 0.000 claims description 6
- IWIUJTLMFKBYLJ-UHFFFAOYSA-N n-[5-chloro-2-[3-[3-(3,4-difluorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1OCC(O)CN1CC(OC=2C=C(F)C(F)=CC=2)CC1 IWIUJTLMFKBYLJ-UHFFFAOYSA-N 0.000 claims description 6
- MFDCXLFWYSMGDK-UHFFFAOYSA-N n-[5-chloro-2-[3-[3-(4-fluorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1OCC(O)CN1CC(OC=2C=CC(F)=CC=2)CC1 MFDCXLFWYSMGDK-UHFFFAOYSA-N 0.000 claims description 6
- 238000002560 therapeutic procedure Methods 0.000 claims description 6
- AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 claims description 5
- 230000003213 activating effect Effects 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- WSGAYMDZRMHRIW-WNPSOCMYSA-N (2s,4s)-1-[3-(2-acetamidophenoxy)-2-hydroxypropyl]-4-(4-chlorophenoxy)pyrrolidine-2-carboxylic acid Chemical compound CC(=O)NC1=CC=CC=C1OCC(O)CN1[C@H](C(O)=O)C[C@H](OC=2C=CC(Cl)=CC=2)C1 WSGAYMDZRMHRIW-WNPSOCMYSA-N 0.000 claims description 4
- 102000009410 Chemokine receptor Human genes 0.000 claims description 4
- 108050000299 Chemokine receptor Proteins 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- NBHJVKZDVXNVEZ-UHFFFAOYSA-N methyl 2-[3-[4-(4-fluorophenoxy)piperidin-1-yl]-2-hydroxypropoxy]benzoate Chemical compound COC(=O)C1=CC=CC=C1OCC(O)CN1CCC(OC=2C=CC(F)=CC=2)CC1 NBHJVKZDVXNVEZ-UHFFFAOYSA-N 0.000 claims description 4
- LYWFPAAUGFSFBA-UHFFFAOYSA-N methyl 2-[[2-[3-[4-(3,4-difluorophenoxy)piperidin-1-yl]-2-hydroxypropoxy]benzoyl]amino]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)NC(=O)C1=CC=CC=C1OCC(O)CN1CCC(OC=2C=C(F)C(F)=CC=2)CC1 LYWFPAAUGFSFBA-UHFFFAOYSA-N 0.000 claims description 4
- UQZSDQYBRFMASZ-NSHGMRRFSA-N n-[2-[(2r)-3-[(2s,4s)-4-(4-chlorophenoxy)-2-(hydroxymethyl)pyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OC[C@H](O)CN1[C@H](CO)C[C@H](OC=2C=CC(Cl)=CC=2)C1 UQZSDQYBRFMASZ-NSHGMRRFSA-N 0.000 claims description 4
- ZDNTWLNRUZPVNW-BPAFIMBUSA-N n-[2-[(2s)-3-[(2r,4s)-4-(4-chlorophenoxy)-2-methylpyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]acetamide Chemical compound C([C@@H](O)CN1C[C@H](C[C@H]1C)OC=1C=CC(Cl)=CC=1)OC1=CC=CC=C1NC(C)=O ZDNTWLNRUZPVNW-BPAFIMBUSA-N 0.000 claims description 4
- UQZSDQYBRFMASZ-BJLQDIEVSA-N n-[2-[(2s)-3-[(2s,4s)-4-(4-chlorophenoxy)-2-(hydroxymethyl)pyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OC[C@@H](O)CN1[C@H](CO)C[C@H](OC=2C=CC(Cl)=CC=2)C1 UQZSDQYBRFMASZ-BJLQDIEVSA-N 0.000 claims description 4
- RTJSEBBDMFDCMK-UHFFFAOYSA-N n-[2-[3-[3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxy-2-methylpropoxy]phenyl]acetamide;hydrochloride Chemical compound Cl.CC(=O)NC1=CC=CC=C1OCC(C)(O)CN1CC(OC=2C=CC(Cl)=CC=2)CC1 RTJSEBBDMFDCMK-UHFFFAOYSA-N 0.000 claims description 4
- GUQYXMSYSJSFHQ-UHFFFAOYSA-N n-[2-[3-[3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]-4,5-difluorophenyl]acetamide Chemical compound CC(=O)NC1=CC(F)=C(F)C=C1OCC(O)CN1CC(OC=2C=CC(Cl)=CC=2)CC1 GUQYXMSYSJSFHQ-UHFFFAOYSA-N 0.000 claims description 4
- WRNUCGIPGKQDBE-UHFFFAOYSA-N n-[2-[3-[3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]-4-methylphenyl]pyrrolidine-1-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CC(OC=2C=CC(Cl)=CC=2)CN1CC(O)COC1=CC(C)=CC=C1NC(=O)N1CCCC1 WRNUCGIPGKQDBE-UHFFFAOYSA-N 0.000 claims description 4
- OYSQIIUDNHUIFD-UHFFFAOYSA-N n-[2-[3-[3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OCC(O)CN1CC(OC=2C=CC(Cl)=CC=2)CC1 OYSQIIUDNHUIFD-UHFFFAOYSA-N 0.000 claims description 4
- LFDJMNIAQQEZJH-UHFFFAOYSA-N n-[2-[3-[3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC=C1OCC(O)CN1CC(OC=2C=CC(Cl)=CC=2)CC1 LFDJMNIAQQEZJH-UHFFFAOYSA-N 0.000 claims description 4
- YKPIXBFBUHCAHL-UHFFFAOYSA-N n-[5-acetyl-2-[3-[3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]acetamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC(=O)NC1=CC(C(C)=O)=CC=C1OCC(O)CN1CC(OC=2C=CC(Cl)=CC=2)CC1 YKPIXBFBUHCAHL-UHFFFAOYSA-N 0.000 claims description 4
- WMTRQBAJSWWKEO-UHFFFAOYSA-N n-[5-chloro-2-[3-[3-[(4-chlorophenyl)methyl]pyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1OCC(O)CN1CC(CC=2C=CC(Cl)=CC=2)CC1 WMTRQBAJSWWKEO-UHFFFAOYSA-N 0.000 claims description 4
- QLLXNJVUUSJAKY-UHFFFAOYSA-N 1-(2,6-dimethoxyphenoxy)-3-[3-(4-fluorophenoxy)pyrrolidin-1-yl]propan-2-ol Chemical compound COC1=CC=CC(OC)=C1OCC(O)CN1CC(OC=2C=CC(F)=CC=2)CC1 QLLXNJVUUSJAKY-UHFFFAOYSA-N 0.000 claims description 3
- MMYDGDYSZZWFSU-UHFFFAOYSA-N 1-(2,6-dimethoxyphenoxy)-3-[4-(4-fluorophenoxy)piperidin-1-yl]propan-2-ol Chemical compound COC1=CC=CC(OC)=C1OCC(O)CN1CCC(OC=2C=CC(F)=CC=2)CC1 MMYDGDYSZZWFSU-UHFFFAOYSA-N 0.000 claims description 3
- TYNSEKHUEZECTJ-UHFFFAOYSA-N 1-(2-aminophenoxy)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propan-2-ol;dihydrochloride Chemical compound Cl.Cl.NC1=CC=CC=C1OCC(O)CN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 TYNSEKHUEZECTJ-UHFFFAOYSA-N 0.000 claims description 3
- VPHFPBPFTWHPDA-UHFFFAOYSA-N 1-[2-[3-[3-(3,4-dichlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]-6-methoxyphenyl]ethanone Chemical compound COC1=CC=CC(OCC(O)CN2CC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1C(C)=O VPHFPBPFTWHPDA-UHFFFAOYSA-N 0.000 claims description 3
- FARBNVQQUGMTBJ-UHFFFAOYSA-N 1-[2-[3-[3-(3,4-dichlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1OCC(O)CN1CC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 FARBNVQQUGMTBJ-UHFFFAOYSA-N 0.000 claims description 3
- SKZRGXXYDAUHQV-UHFFFAOYSA-N 1-[2-[3-[3-(3,4-dichlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]propan-1-one Chemical compound CCC(=O)C1=CC=CC=C1OCC(O)CN1CC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 SKZRGXXYDAUHQV-UHFFFAOYSA-N 0.000 claims description 3
- FPYFITADEVYXHT-UHFFFAOYSA-N 1-[2-[3-[3-(3,4-difluorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]-6-methoxyphenyl]ethanone Chemical compound COC1=CC=CC(OCC(O)CN2CC(CC2)OC=2C=C(F)C(F)=CC=2)=C1C(C)=O FPYFITADEVYXHT-UHFFFAOYSA-N 0.000 claims description 3
- QHFFUNPIGPVCDI-UHFFFAOYSA-N 1-[2-[3-[3-(3,4-difluorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1OCC(O)CN1CC(OC=2C=C(F)C(F)=CC=2)CC1 QHFFUNPIGPVCDI-UHFFFAOYSA-N 0.000 claims description 3
- JIJJDGGSHVPGGS-UHFFFAOYSA-N 1-[2-[3-[3-(3,4-difluorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]propan-1-one Chemical compound CCC(=O)C1=CC=CC=C1OCC(O)CN1CC(OC=2C=C(F)C(F)=CC=2)CC1 JIJJDGGSHVPGGS-UHFFFAOYSA-N 0.000 claims description 3
- TXUJOWGKGLIRIX-UHFFFAOYSA-N 1-[2-[3-[3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]-6-methoxyphenyl]ethanone Chemical compound COC1=CC=CC(OCC(O)CN2CC(CC2)OC=2C=CC(Cl)=CC=2)=C1C(C)=O TXUJOWGKGLIRIX-UHFFFAOYSA-N 0.000 claims description 3
- RKQLPFAALCGXDA-UHFFFAOYSA-N 1-[2-[3-[3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]-3-methylurea;hydrochloride Chemical compound Cl.CNC(=O)NC1=CC=CC=C1OCC(O)CN1CC(OC=2C=CC(Cl)=CC=2)CC1 RKQLPFAALCGXDA-UHFFFAOYSA-N 0.000 claims description 3
- RDOMSIRDJMZQFG-UHFFFAOYSA-N 1-[2-[3-[3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1OCC(O)CN1CC(OC=2C=CC(Cl)=CC=2)CC1 RDOMSIRDJMZQFG-UHFFFAOYSA-N 0.000 claims description 3
- SXGHXBQJMAXRGT-UHFFFAOYSA-N 1-[2-[3-[3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]propan-1-one Chemical compound CCC(=O)C1=CC=CC=C1OCC(O)CN1CC(OC=2C=CC(Cl)=CC=2)CC1 SXGHXBQJMAXRGT-UHFFFAOYSA-N 0.000 claims description 3
- JXQDUZVYMKOKRE-UHFFFAOYSA-N 1-[2-[3-[3-(4-fluorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]-6-methoxyphenyl]ethanone Chemical compound COC1=CC=CC(OCC(O)CN2CC(CC2)OC=2C=CC(F)=CC=2)=C1C(C)=O JXQDUZVYMKOKRE-UHFFFAOYSA-N 0.000 claims description 3
- MXPVPZCHHMRENY-UHFFFAOYSA-N 1-[2-[3-[3-(4-fluorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1OCC(O)CN1CC(OC=2C=CC(F)=CC=2)CC1 MXPVPZCHHMRENY-UHFFFAOYSA-N 0.000 claims description 3
- JOEULLYUHDUFMK-UHFFFAOYSA-N 1-[2-[3-[3-(4-fluorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]propan-1-one Chemical compound CCC(=O)C1=CC=CC=C1OCC(O)CN1CC(OC=2C=CC(F)=CC=2)CC1 JOEULLYUHDUFMK-UHFFFAOYSA-N 0.000 claims description 3
- GGWSASHPIBJZDS-UHFFFAOYSA-N 1-[2-[3-[3-[(4-chlorophenoxy)methyl]piperidin-1-yl]-2-hydroxypropoxy]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1OCC(O)CN1CC(COC=2C=CC(Cl)=CC=2)CCC1 GGWSASHPIBJZDS-UHFFFAOYSA-N 0.000 claims description 3
- SGHOVYLSVRVHHR-UHFFFAOYSA-N 1-[2-[3-[3-[(4-chlorophenoxy)methyl]piperidin-1-yl]-2-hydroxypropoxy]phenyl]propan-1-one Chemical compound CCC(=O)C1=CC=CC=C1OCC(O)CN1CC(COC=2C=CC(Cl)=CC=2)CCC1 SGHOVYLSVRVHHR-UHFFFAOYSA-N 0.000 claims description 3
- DKWBIRJXBULLGN-UHFFFAOYSA-N 1-[2-[3-[3-[(4-fluorophenoxy)methyl]piperidin-1-yl]-2-hydroxypropoxy]-6-methoxyphenyl]ethanone Chemical compound COC1=CC=CC(OCC(O)CN2CC(COC=3C=CC(F)=CC=3)CCC2)=C1C(C)=O DKWBIRJXBULLGN-UHFFFAOYSA-N 0.000 claims description 3
- ZAXDUQFHPFUJNF-UHFFFAOYSA-N 1-[2-[3-[3-[(4-fluorophenoxy)methyl]piperidin-1-yl]-2-hydroxypropoxy]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1OCC(O)CN1CC(COC=2C=CC(F)=CC=2)CCC1 ZAXDUQFHPFUJNF-UHFFFAOYSA-N 0.000 claims description 3
- XHGDGEDAPFJBII-UHFFFAOYSA-N 1-[2-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropoxy]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1OCC(O)CN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 XHGDGEDAPFJBII-UHFFFAOYSA-N 0.000 claims description 3
- CLRMKSASWXDYCE-UHFFFAOYSA-N 1-[2-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropoxy]phenyl]propan-1-one Chemical compound CCC(=O)C1=CC=CC=C1OCC(O)CN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 CLRMKSASWXDYCE-UHFFFAOYSA-N 0.000 claims description 3
- AQCJGADHNWETLJ-UHFFFAOYSA-N 1-[2-[3-[4-(3,4-difluorophenoxy)piperidin-1-yl]-2-hydroxypropoxy]phenyl]propan-1-one Chemical compound CCC(=O)C1=CC=CC=C1OCC(O)CN1CCC(OC=2C=C(F)C(F)=CC=2)CC1 AQCJGADHNWETLJ-UHFFFAOYSA-N 0.000 claims description 3
- QHRFWGPGUXDOIE-UHFFFAOYSA-N 1-[2-[3-[4-(4-chlorophenoxy)piperidin-1-yl]-2-hydroxypropoxy]-6-methoxyphenyl]ethanone Chemical compound COC1=CC=CC(OCC(O)CN2CCC(CC2)OC=2C=CC(Cl)=CC=2)=C1C(C)=O QHRFWGPGUXDOIE-UHFFFAOYSA-N 0.000 claims description 3
- UQEOYVUGRXXDLM-UHFFFAOYSA-N 1-[2-[3-[4-(4-chlorophenoxy)piperidin-1-yl]-2-hydroxypropoxy]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1OCC(O)CN1CCC(OC=2C=CC(Cl)=CC=2)CC1 UQEOYVUGRXXDLM-UHFFFAOYSA-N 0.000 claims description 3
- RRPBPXKIFGTTCU-UHFFFAOYSA-N 1-[2-[3-[4-(4-chlorophenoxy)piperidin-1-yl]-2-hydroxypropoxy]phenyl]propan-1-one Chemical compound CCC(=O)C1=CC=CC=C1OCC(O)CN1CCC(OC=2C=CC(Cl)=CC=2)CC1 RRPBPXKIFGTTCU-UHFFFAOYSA-N 0.000 claims description 3
- SNLFCYMYNRABCI-UHFFFAOYSA-N 1-[2-[3-[4-(4-fluorophenoxy)piperidin-1-yl]-2-hydroxypropoxy]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1OCC(O)CN1CCC(OC=2C=CC(F)=CC=2)CC1 SNLFCYMYNRABCI-UHFFFAOYSA-N 0.000 claims description 3
- FXIQFPJIRUOHNZ-UHFFFAOYSA-N 1-[2-[3-[4-(4-fluorophenoxy)piperidin-1-yl]-2-hydroxypropoxy]phenyl]propan-1-one Chemical compound CCC(=O)C1=CC=CC=C1OCC(O)CN1CCC(OC=2C=CC(F)=CC=2)CC1 FXIQFPJIRUOHNZ-UHFFFAOYSA-N 0.000 claims description 3
- QJXVMCMSNPYFAY-UHFFFAOYSA-N 1-[3-(3,4-dichlorophenoxy)pyrrolidin-1-yl]-3-(2-methoxyphenoxy)propan-2-ol Chemical compound COC1=CC=CC=C1OCC(O)CN1CC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 QJXVMCMSNPYFAY-UHFFFAOYSA-N 0.000 claims description 3
- RGVRNVVPHMGSRP-UHFFFAOYSA-N 1-[3-(3,4-difluorophenoxy)pyrrolidin-1-yl]-3-(2-methoxyphenoxy)propan-2-ol Chemical compound COC1=CC=CC=C1OCC(O)CN1CC(OC=2C=C(F)C(F)=CC=2)CC1 RGVRNVVPHMGSRP-UHFFFAOYSA-N 0.000 claims description 3
- QVMUMFLLVWORJV-UHFFFAOYSA-N 1-[3-(4-chlorophenoxy)pyrrolidin-1-yl]-3-(2,6-dimethoxyphenoxy)propan-2-ol Chemical compound COC1=CC=CC(OC)=C1OCC(O)CN1CC(OC=2C=CC(Cl)=CC=2)CC1 QVMUMFLLVWORJV-UHFFFAOYSA-N 0.000 claims description 3
- AKWIFIHWWBVSPE-UHFFFAOYSA-N 1-[3-(4-chlorophenoxy)pyrrolidin-1-yl]-3-(2-methoxyphenoxy)propan-2-ol Chemical compound COC1=CC=CC=C1OCC(O)CN1CC(OC=2C=CC(Cl)=CC=2)CC1 AKWIFIHWWBVSPE-UHFFFAOYSA-N 0.000 claims description 3
- BFWIUIIIURTQDH-UHFFFAOYSA-N 1-[3-(4-fluorophenoxy)pyrrolidin-1-yl]-3-(2-methoxyphenoxy)propan-2-ol Chemical compound COC1=CC=CC=C1OCC(O)CN1CC(OC=2C=CC(F)=CC=2)CC1 BFWIUIIIURTQDH-UHFFFAOYSA-N 0.000 claims description 3
- YQTSGGHLBASULT-UHFFFAOYSA-N 1-[3-[(4-fluorophenoxy)methyl]piperidin-1-yl]-3-(2-methoxyphenoxy)propan-2-ol Chemical compound COC1=CC=CC=C1OCC(O)CN1CC(COC=2C=CC(F)=CC=2)CCC1 YQTSGGHLBASULT-UHFFFAOYSA-N 0.000 claims description 3
- GBASVMVTEROLAF-UHFFFAOYSA-N 1-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-3-(2,6-dimethoxyphenoxy)propan-2-ol Chemical compound COC1=CC=CC(OC)=C1OCC(O)CN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 GBASVMVTEROLAF-UHFFFAOYSA-N 0.000 claims description 3
- UXLKCLQLCDPLQN-UHFFFAOYSA-N 1-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-3-(2-methoxyphenoxy)propan-2-ol Chemical compound COC1=CC=CC=C1OCC(O)CN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 UXLKCLQLCDPLQN-UHFFFAOYSA-N 0.000 claims description 3
- LQTHERZCUCWRHG-UHFFFAOYSA-N 1-[4-(4-chlorophenoxy)piperidin-1-yl]-3-(2-methoxyphenoxy)propan-2-ol Chemical compound COC1=CC=CC=C1OCC(O)CN1CCC(OC=2C=CC(Cl)=CC=2)CC1 LQTHERZCUCWRHG-UHFFFAOYSA-N 0.000 claims description 3
- YBZLGBDIUOVESN-UHFFFAOYSA-N 1-[4-(4-fluorophenoxy)piperidin-1-yl]-3-(2-methoxyphenoxy)propan-2-ol Chemical compound COC1=CC=CC=C1OCC(O)CN1CCC(OC=2C=CC(F)=CC=2)CC1 YBZLGBDIUOVESN-UHFFFAOYSA-N 0.000 claims description 3
- AKWLTUQSXWGQMU-UHFFFAOYSA-N 1-[5-chloro-2-[3-[4-(4-chlorobenzoyl)piperazin-1-yl]-2-hydroxypropoxy]phenyl]ethanone Chemical compound CC(=O)C1=CC(Cl)=CC=C1OCC(O)CN1CCN(C(=O)C=2C=CC(Cl)=CC=2)CC1 AKWLTUQSXWGQMU-UHFFFAOYSA-N 0.000 claims description 3
- AAQPRMBFQMBKCJ-UHFFFAOYSA-N 2-[3-[3-(3,4-difluorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1OCC(O)CN1CC(OC=2C=C(F)C(F)=CC=2)CC1 AAQPRMBFQMBKCJ-UHFFFAOYSA-N 0.000 claims description 3
- QYJXEAZIMHMEEY-UHFFFAOYSA-N 2-[3-[3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1OCC(O)CN1CC(OC=2C=CC(Cl)=CC=2)CC1 QYJXEAZIMHMEEY-UHFFFAOYSA-N 0.000 claims description 3
- SEUICBCZMZFZBX-UHFFFAOYSA-N 2-[3-[3-(4-cyanophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1OCC(O)CN1CC(OC=2C=CC(=CC=2)C#N)CC1 SEUICBCZMZFZBX-UHFFFAOYSA-N 0.000 claims description 3
- VGEAKGVEESETKL-UHFFFAOYSA-N 2-[3-[3-(4-fluorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1OCC(O)CN1CC(OC=2C=CC(F)=CC=2)CC1 VGEAKGVEESETKL-UHFFFAOYSA-N 0.000 claims description 3
- LZRQUVROKOYOKI-UHFFFAOYSA-N 2-[3-[3-[(4-chlorophenoxy)methyl]piperidin-1-yl]-2-hydroxypropoxy]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1OCC(O)CN1CC(COC=2C=CC(Cl)=CC=2)CCC1 LZRQUVROKOYOKI-UHFFFAOYSA-N 0.000 claims description 3
- RQGURKMXKITTSG-UHFFFAOYSA-N 2-[3-[3-[(4-fluorophenoxy)methyl]piperidin-1-yl]-2-hydroxypropoxy]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1OCC(O)CN1CC(COC=2C=CC(F)=CC=2)CCC1 RQGURKMXKITTSG-UHFFFAOYSA-N 0.000 claims description 3
- DNNXBZJPRXQNBZ-UHFFFAOYSA-N 2-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropoxy]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1OCC(O)CN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 DNNXBZJPRXQNBZ-UHFFFAOYSA-N 0.000 claims description 3
- YZQFHSSAYSQXAV-UHFFFAOYSA-N 2-[3-[4-(3,4-difluorophenoxy)piperidin-1-yl]-2-hydroxypropoxy]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1OCC(O)CN1CCC(OC=2C=C(F)C(F)=CC=2)CC1 YZQFHSSAYSQXAV-UHFFFAOYSA-N 0.000 claims description 3
- JWWRFTZGEXUHEH-UHFFFAOYSA-N 2-[3-[4-(4-chlorophenoxy)piperidin-1-yl]-2-hydroxypropoxy]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1OCC(O)CN1CCC(OC=2C=CC(Cl)=CC=2)CC1 JWWRFTZGEXUHEH-UHFFFAOYSA-N 0.000 claims description 3
- QKHNYMKYBXIVNC-UHFFFAOYSA-N 2-[3-[4-(4-fluorophenoxy)piperidin-1-yl]-2-hydroxypropoxy]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1OCC(O)CN1CCC(OC=2C=CC(F)=CC=2)CC1 QKHNYMKYBXIVNC-UHFFFAOYSA-N 0.000 claims description 3
- SBXZAQNQZBKHMX-UHFFFAOYSA-N 3-[2-[3-[3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]-4-methylphenyl]-1,1-dimethylurea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CN(C)C(=O)NC1=CC=C(C)C=C1OCC(O)CN1CC(OC=2C=CC(Cl)=CC=2)CC1 SBXZAQNQZBKHMX-UHFFFAOYSA-N 0.000 claims description 3
- NRMGSPWZPSIZJU-UHFFFAOYSA-N 4-[1-[2-hydroxy-3-(2-propanoylphenoxy)propyl]pyrrolidin-3-yl]oxybenzonitrile Chemical compound CCC(=O)C1=CC=CC=C1OCC(O)CN1CC(OC=2C=CC(=CC=2)C#N)CC1 NRMGSPWZPSIZJU-UHFFFAOYSA-N 0.000 claims description 3
- UWDMKTDPDJCJOP-UHFFFAOYSA-N 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-carboxylate Chemical compound CC1(C)CC(O)(C(O)=O)CC(C)(C)N1 UWDMKTDPDJCJOP-UHFFFAOYSA-N 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- OYSQIIUDNHUIFD-PKOBYXMFSA-N N-[2-[(2S)-3-[(3R)-3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]acetamide Chemical compound C(C)(=O)NC1=C(C=CC=C1)OC[C@H](CN1C[C@@H](CC1)OC1=CC=C(C=C1)Cl)O OYSQIIUDNHUIFD-PKOBYXMFSA-N 0.000 claims description 3
- SMDBHZQHRPQMQQ-OGOMYWKWSA-N ethyl (2s,4s)-1-[3-(2-acetamidophenoxy)-2-hydroxypropyl]-4-(3,4-dichlorophenoxy)pyrrolidine-2-carboxylate Chemical compound C([C@H](C[C@H]1C(=O)OCC)OC=2C=C(Cl)C(Cl)=CC=2)N1CC(O)COC1=CC=CC=C1NC(C)=O SMDBHZQHRPQMQQ-OGOMYWKWSA-N 0.000 claims description 3
- TZWAHAICMKJIAK-UHFFFAOYSA-N methyl 2-[[2-[3-[3-(3,4-dichlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]benzoyl]amino]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)NC(=O)C1=CC=CC=C1OCC(O)CN1CC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 TZWAHAICMKJIAK-UHFFFAOYSA-N 0.000 claims description 3
- KCCQNRMPLZQBNY-UHFFFAOYSA-N methyl 2-[[2-[3-[3-(3,4-dichlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]benzoyl]amino]acetate Chemical compound COC(=O)CNC(=O)C1=CC=CC=C1OCC(O)CN1CC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 KCCQNRMPLZQBNY-UHFFFAOYSA-N 0.000 claims description 3
- MXJURQMLRCSLNO-UHFFFAOYSA-N methyl 2-[[2-[3-[3-(3,4-difluorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]benzoyl]amino]acetate Chemical compound COC(=O)CNC(=O)C1=CC=CC=C1OCC(O)CN1CC(OC=2C=C(F)C(F)=CC=2)CC1 MXJURQMLRCSLNO-UHFFFAOYSA-N 0.000 claims description 3
- ITTHNWIVJRLOLO-UHFFFAOYSA-N methyl 2-[[2-[3-[3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]benzoyl]amino]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)NC(=O)C1=CC=CC=C1OCC(O)CN1CC(OC=2C=CC(Cl)=CC=2)CC1 ITTHNWIVJRLOLO-UHFFFAOYSA-N 0.000 claims description 3
- LPBKOUDEQGSXLH-UHFFFAOYSA-N methyl 2-[[2-[3-[3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]benzoyl]amino]acetate Chemical compound COC(=O)CNC(=O)C1=CC=CC=C1OCC(O)CN1CC(OC=2C=CC(Cl)=CC=2)CC1 LPBKOUDEQGSXLH-UHFFFAOYSA-N 0.000 claims description 3
- DVEZRDFJNCHBBZ-UHFFFAOYSA-N methyl 2-[[2-[3-[3-(4-cyanophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]benzoyl]amino]acetate Chemical compound COC(=O)CNC(=O)C1=CC=CC=C1OCC(O)CN1CC(OC=2C=CC(=CC=2)C#N)CC1 DVEZRDFJNCHBBZ-UHFFFAOYSA-N 0.000 claims description 3
- SJHKDUFERPKWDB-UHFFFAOYSA-N methyl 2-[[2-[3-[3-(4-fluorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]benzoyl]amino]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)NC(=O)C1=CC=CC=C1OCC(O)CN1CC(OC=2C=CC(F)=CC=2)CC1 SJHKDUFERPKWDB-UHFFFAOYSA-N 0.000 claims description 3
- BRHWKZMRINCYQP-UHFFFAOYSA-N methyl 2-[[2-[3-[3-(4-fluorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]benzoyl]amino]acetate Chemical compound COC(=O)CNC(=O)C1=CC=CC=C1OCC(O)CN1CC(OC=2C=CC(F)=CC=2)CC1 BRHWKZMRINCYQP-UHFFFAOYSA-N 0.000 claims description 3
- BUIKRYWWJSHSLE-UHFFFAOYSA-N methyl 2-[[2-[3-[3-[(4-chlorophenoxy)methyl]piperidin-1-yl]-2-hydroxypropoxy]benzoyl]amino]acetate Chemical compound COC(=O)CNC(=O)C1=CC=CC=C1OCC(O)CN1CC(COC=2C=CC(Cl)=CC=2)CCC1 BUIKRYWWJSHSLE-UHFFFAOYSA-N 0.000 claims description 3
- NFPPXLRBAGZBMG-UHFFFAOYSA-N methyl 2-[[2-[3-[3-[(4-fluorophenoxy)methyl]piperidin-1-yl]-2-hydroxypropoxy]benzoyl]amino]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)NC(=O)C1=CC=CC=C1OCC(O)CN1CC(COC=2C=CC(F)=CC=2)CCC1 NFPPXLRBAGZBMG-UHFFFAOYSA-N 0.000 claims description 3
- GNGCKTIWOSSTJN-UHFFFAOYSA-N methyl 2-[[2-[3-[4-(3,4-difluorophenoxy)piperidin-1-yl]-2-hydroxypropoxy]benzoyl]amino]acetate Chemical compound COC(=O)CNC(=O)C1=CC=CC=C1OCC(O)CN1CCC(OC=2C=C(F)C(F)=CC=2)CC1 GNGCKTIWOSSTJN-UHFFFAOYSA-N 0.000 claims description 3
- XGBORGQAOKFWQS-UHFFFAOYSA-N methyl 2-[[2-[3-[4-(4-chlorophenoxy)piperidin-1-yl]-2-hydroxypropoxy]benzoyl]amino]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)NC(=O)C1=CC=CC=C1OCC(O)CN1CCC(OC=2C=CC(Cl)=CC=2)CC1 XGBORGQAOKFWQS-UHFFFAOYSA-N 0.000 claims description 3
- GHEVXOJVKXRIOT-UHFFFAOYSA-N methyl 2-[[2-[3-[4-(4-chlorophenoxy)piperidin-1-yl]-2-hydroxypropoxy]benzoyl]amino]acetate Chemical compound COC(=O)CNC(=O)C1=CC=CC=C1OCC(O)CN1CCC(OC=2C=CC(Cl)=CC=2)CC1 GHEVXOJVKXRIOT-UHFFFAOYSA-N 0.000 claims description 3
- XILVPBNPAZQANO-UHFFFAOYSA-N methyl 2-[[2-[3-[4-(4-fluorophenoxy)piperidin-1-yl]-2-hydroxypropoxy]benzoyl]amino]acetate Chemical compound COC(=O)CNC(=O)C1=CC=CC=C1OCC(O)CN1CCC(OC=2C=CC(F)=CC=2)CC1 XILVPBNPAZQANO-UHFFFAOYSA-N 0.000 claims description 3
- FDGQIBXNXOYNNU-UHFFFAOYSA-N methyl 3-[2-[3-[3-(3,4-dichlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]propanoate Chemical compound COC(=O)CCC1=CC=CC=C1OCC(O)CN1CC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 FDGQIBXNXOYNNU-UHFFFAOYSA-N 0.000 claims description 3
- NBXFCOPAJLTBHC-UHFFFAOYSA-N methyl 3-[2-[3-[3-(3,4-difluorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]propanoate Chemical compound COC(=O)CCC1=CC=CC=C1OCC(O)CN1CC(OC=2C=C(F)C(F)=CC=2)CC1 NBXFCOPAJLTBHC-UHFFFAOYSA-N 0.000 claims description 3
- PKOSZUPRPIRFIF-UHFFFAOYSA-N methyl 3-[2-[3-[3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]propanoate Chemical compound COC(=O)CCC1=CC=CC=C1OCC(O)CN1CC(OC=2C=CC(Cl)=CC=2)CC1 PKOSZUPRPIRFIF-UHFFFAOYSA-N 0.000 claims description 3
- BBHXPXRFRIRJTD-UHFFFAOYSA-N methyl 3-[2-[3-[3-(4-cyanophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]propanoate Chemical compound COC(=O)CCC1=CC=CC=C1OCC(O)CN1CC(OC=2C=CC(=CC=2)C#N)CC1 BBHXPXRFRIRJTD-UHFFFAOYSA-N 0.000 claims description 3
- MRVWUOPLHITFDN-UHFFFAOYSA-N methyl 3-[2-[3-[3-(4-fluorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]propanoate Chemical compound COC(=O)CCC1=CC=CC=C1OCC(O)CN1CC(OC=2C=CC(F)=CC=2)CC1 MRVWUOPLHITFDN-UHFFFAOYSA-N 0.000 claims description 3
- FXPPIQTZVMVFES-UHFFFAOYSA-N methyl 3-[2-[3-[3-[(4-chlorophenoxy)methyl]piperidin-1-yl]-2-hydroxypropoxy]phenyl]propanoate Chemical compound COC(=O)CCC1=CC=CC=C1OCC(O)CN1CC(COC=2C=CC(Cl)=CC=2)CCC1 FXPPIQTZVMVFES-UHFFFAOYSA-N 0.000 claims description 3
- DESICZZGJAOXGA-UHFFFAOYSA-N methyl 3-[2-[3-[3-[(4-fluorophenoxy)methyl]piperidin-1-yl]-2-hydroxypropoxy]phenyl]propanoate Chemical compound COC(=O)CCC1=CC=CC=C1OCC(O)CN1CC(COC=2C=CC(F)=CC=2)CCC1 DESICZZGJAOXGA-UHFFFAOYSA-N 0.000 claims description 3
- BMUFQTUSRHYBME-UHFFFAOYSA-N methyl 3-[2-[3-[4-(3,4-difluorophenoxy)piperidin-1-yl]-2-hydroxypropoxy]phenyl]propanoate Chemical compound COC(=O)CCC1=CC=CC=C1OCC(O)CN1CCC(OC=2C=C(F)C(F)=CC=2)CC1 BMUFQTUSRHYBME-UHFFFAOYSA-N 0.000 claims description 3
- CWDJLXQIDVZQDR-UHFFFAOYSA-N methyl 3-[2-[3-[4-(4-chlorophenoxy)piperidin-1-yl]-2-hydroxypropoxy]phenyl]propanoate Chemical compound COC(=O)CCC1=CC=CC=C1OCC(O)CN1CCC(OC=2C=CC(Cl)=CC=2)CC1 CWDJLXQIDVZQDR-UHFFFAOYSA-N 0.000 claims description 3
- YZVNDBXUNUQOLW-UHFFFAOYSA-N methyl 3-[2-[3-[4-(4-fluorophenoxy)piperidin-1-yl]-2-hydroxypropoxy]phenyl]propanoate Chemical compound COC(=O)CCC1=CC=CC=C1OCC(O)CN1CCC(OC=2C=CC(F)=CC=2)CC1 YZVNDBXUNUQOLW-UHFFFAOYSA-N 0.000 claims description 3
- NIDMBYPVESCCIN-UHFFFAOYSA-N methyl 4-acetamido-3-[3-[3-(3,4-dichlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]benzoate Chemical compound COC(=O)C1=CC=C(NC(C)=O)C(OCC(O)CN2CC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 NIDMBYPVESCCIN-UHFFFAOYSA-N 0.000 claims description 3
- LTEBHGJIUUPQCP-UHFFFAOYSA-N methyl 4-acetamido-3-[3-[3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]benzoate Chemical compound COC(=O)C1=CC=C(NC(C)=O)C(OCC(O)CN2CC(CC2)OC=2C=CC(Cl)=CC=2)=C1 LTEBHGJIUUPQCP-UHFFFAOYSA-N 0.000 claims description 3
- OHJZBRBQXJQQGM-NQAVQENRSA-N n-[2-[(1r,2s,3r)-3-[(3s)-3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxycyclopentyl]oxy-4-hydroxyphenyl]acetamide Chemical compound CC(=O)NC1=CC=C(O)C=C1O[C@H]1[C@@H](O)[C@H](N2C[C@H](CC2)OC=2C=CC(Cl)=CC=2)CC1 OHJZBRBQXJQQGM-NQAVQENRSA-N 0.000 claims description 3
- OHJZBRBQXJQQGM-XHRGMSINSA-N n-[2-[(1s,2r,3s)-3-[(3s)-3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxycyclopentyl]oxy-4-hydroxyphenyl]acetamide Chemical compound CC(=O)NC1=CC=C(O)C=C1O[C@@H]1[C@H](O)[C@@H](N2C[C@H](CC2)OC=2C=CC(Cl)=CC=2)CC1 OHJZBRBQXJQQGM-XHRGMSINSA-N 0.000 claims description 3
- QGQKHHXQNNPDED-UZVYXBEXSA-N n-[2-[(1s,2r,3s)-3-[(3s)-3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxycyclopentyl]oxyphenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1O[C@@H]1[C@H](O)[C@@H](N2C[C@H](CC2)OC=2C=CC(Cl)=CC=2)CC1 QGQKHHXQNNPDED-UZVYXBEXSA-N 0.000 claims description 3
- ZCGQELYDYMAKCP-MJGOQNOKSA-N n-[2-[(2r)-3-[(3s)-3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]-4-fluorophenyl]acetamide Chemical compound CC(=O)NC1=CC=C(F)C=C1OC[C@H](O)CN1C[C@@H](OC=2C=CC(Cl)=CC=2)CC1 ZCGQELYDYMAKCP-MJGOQNOKSA-N 0.000 claims description 3
- FTDCMDKDIGWKID-DCPHZVHLSA-N n-[2-[(2s)-3-[(2s,4s)-4-(4-chlorophenoxy)-2-methylpyrrolidin-1-yl]-2-hydroxypropoxy]-4-fluorophenyl]acetamide Chemical compound C([C@@H](O)CN1C[C@H](C[C@@H]1C)OC=1C=CC(Cl)=CC=1)OC1=CC(F)=CC=C1NC(C)=O FTDCMDKDIGWKID-DCPHZVHLSA-N 0.000 claims description 3
- ZCGQELYDYMAKCP-PKOBYXMFSA-N n-[2-[(2s)-3-[(3r)-3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]-4-fluorophenyl]acetamide Chemical compound CC(=O)NC1=CC=C(F)C=C1OC[C@@H](O)CN1C[C@H](OC=2C=CC(Cl)=CC=2)CC1 ZCGQELYDYMAKCP-PKOBYXMFSA-N 0.000 claims description 3
- ZCGQELYDYMAKCP-HKUYNNGSSA-N n-[2-[(2s)-3-[(3s)-3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]-4-fluorophenyl]acetamide Chemical compound CC(=O)NC1=CC=C(F)C=C1OC[C@@H](O)CN1C[C@@H](OC=2C=CC(Cl)=CC=2)CC1 ZCGQELYDYMAKCP-HKUYNNGSSA-N 0.000 claims description 3
- ZDHUCNWQOIIMMU-HKUYNNGSSA-N n-[2-[(2s)-3-[(3s)-3-(4-chlorophenoxy)pyrrolidin-1-yl]-2-hydroxypropoxy]-4-hydroxyphenyl]acetamide Chemical compound CC(=O)NC1=CC=C(O)C=C1OC[C@@H](O)CN1C[C@@H](OC=2C=CC(Cl)=CC=2)CC1 ZDHUCNWQOIIMMU-HKUYNNGSSA-N 0.000 claims description 3
- NZRCPNJOFMGJPO-UHFFFAOYSA-N n-[2-[2-hydroxy-3-[3-(4-methoxyphenoxy)pyrrolidin-1-yl]propoxy]phenyl]acetamide Chemical compound C1=CC(OC)=CC=C1OC1CN(CC(O)COC=2C(=CC=CC=2)NC(C)=O)CC1 NZRCPNJOFMGJPO-UHFFFAOYSA-N 0.000 claims description 3
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- JLWNHLZHRDWCAE-ZFWWWQNUSA-N tert-butyl (2s,4s)-4-(4-chlorophenoxy)-2-(methylsulfonyloxymethyl)pyrrolidine-1-carboxylate Chemical compound C1[C@@H](COS(C)(=O)=O)N(C(=O)OC(C)(C)C)C[C@H]1OC1=CC=C(Cl)C=C1 JLWNHLZHRDWCAE-ZFWWWQNUSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D207/14—Nitrogen atoms not forming part of a nitro radical
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- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
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- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
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- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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FR2802533B1 (fr) | 1999-12-17 | 2002-02-15 | Sanofi Synthelabo | Phenoxypropanolamines, leur preparation et leur application en therapeutique |
CO5300399A1 (es) | 2000-02-25 | 2003-07-31 | Astrazeneca Ab | Heterocicliocs que contienen nitrogeno, proceso para su preparacion y composiciones farmaceuticas que los contienen |
GB0011838D0 (en) | 2000-05-17 | 2000-07-05 | Astrazeneca Ab | Chemical compounds |
AR028948A1 (es) | 2000-06-20 | 2003-05-28 | Astrazeneca Ab | Compuestos novedosos |
AR028947A1 (es) * | 2000-06-20 | 2003-05-28 | Astrazeneca Ab | Compuestos novedosos |
US7005439B2 (en) | 2000-06-20 | 2006-02-28 | Astrazeneca Ab | Compounds |
SE0100903D0 (sv) | 2001-03-15 | 2001-03-15 | Astrazeneca Ab | Compounds |
SE0101038D0 (sv) | 2001-03-23 | 2001-03-23 | Astrazeneca Ab | Novel compounds |
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2001
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